New computer same ipod ipod not working

I recently purchased a new laptop. It has been authorized (after several attempts because the "iTunes Store was unavailable") and now my iPod, which I have had for several years and has successfully been working no longer properly syncs with the new laptop.
When I synced iTunes told me that audiobooks that I had on the iPod and was listening to no longer worked with the iPod. This makes absolutely no sense. They worked on the iPod earlier this week before I synced it through the new laptop. How do I recover the ability to listen to songs and books that previously had no issues on my iPod?
I have also lost all of my playlists, this has never happened before and I have changed computers several times with this particular iPod.

Peter,
Welcome to Apple Discussions.
First: It is not safe to have your music on your iPod only. iPods do fail sometimes and would leave you with an empty iPod and no music.
That said, it is possible to get your tunes of your iPod. You don't mention your OS but you may find an utility for this on versiontracker.
iPod Agent (windows).
Senuti (Mac).
JJ
Don't steal music !! Just a statement, not an accusation

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http://support.apple.com/kb/HT4527
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Removing and reinstalling iTunes and other software components for Windows Vista, Windows 7, or Windows 8
http://support.apple.com/kb/HT1923?viewlocale=en_US
Issues installing iTunes or QuickTime for Windows
http://support.apple.com/kb/ht1926
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New computer same ipod ipod not working

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